Why Good Teams Struggle (and What to Do About It)
2,714 words in this newsletter - about 11 minutes and 25 seconds to read.
Guest Editor: Karla Peralta
At Cityfi, we often hear organizations explain dysfunction with one word: culture. But “culture” is not a catch-all diagnosis. It’s tempting to stop there, blaming values, morale, or attitudes when teams hit friction. The truth is more practical: good teams struggle when clarity, communication, roles, and tools are missing.
This month’s newsletter challenges some of the biggest misconceptions around why organizations falter and offers concrete strategies to help them thrive. Each article unpacks a different piece of the puzzle:
It’s Not (Just) Culture: Diagnosing What’s Really Broken by Senior Principal Camron Bridgford reminds us that culture is often the symptom, not the root cause. Drawing on Cityfi’s organizational assessment work, she shows how challenges usually stem from a lack of clarity, in vision, roles, processes, and tools. By unearthing where clarity is missing, organizations can restore agency, motivation, and creativity across teams.
Communicating Change: Bringing People Along and Building Buy-In by Partner Story Bellows explores how thoughtful internal communication and narrative can make change less intimidating and more collaborative, building the trust needed for transformation.
Designing for Efficiency: Process, Tools, and Ownership by me (Karla Peralta) takes on the meaning of “efficiency.” We look at how to examine repetitive tasks, leverage automation and AI to free up brainspace, and decide what should be delegated, streamlined, or reimagined.
Making Space to Think Big: Why Teams Need Time to Imagine by Senior Associate Carolina de Urquijo Isoard highlights how creativity isn’t a luxury, but a necessity. Without intentional room to reflect, experiment, and dream, even the most capable teams get stuck in daily operations.
How Clear Vision, Processes, and Tools Drive Special Event Mobility Success by Senior Associate Monique Ho shows these principles in action. From MLB All-Star Week in Seattle to stadium operations in Atlanta, the key to success wasn’t culture - it was clarity, process, and shared tools.
Taken together, these perspectives point to a simple but powerful truth: strong teams are built through structure, clarity, and trust. When vision and roles are defined, communication is intentional, and tools are thoughtfully applied, culture follows, not the other way around.
We’d love to talk with you, not only when challenges arise, but also when you want to push boundaries, create space for innovation, and make sure your staff feels empowered to achieve your mission.
It’s Not (Just) Culture: Diagnosing What’s Really Broken
Human beings are complex (did I even need to tell you this?). Every person holds a worldview shaped by their unique values and motivations. Our drives, interests, and curiosities are a reflection of our learned experiences and innate personalities. This is evident within families - where we are part of an ecosystem that, well, we didn’t necessarily choose. The workplace is another area where, while we do exert some control over who we work for and with, there are also factors out of our control that shape our day-to-day experience in our jobs, and therefore, have an impact on our productivity, creativity, and efficiency.
The first and natural inclination in a work environment that feels like it’s not living up to its potential is to blame “the culture.” There is certainly truth to this, but culture is complex, can feel ambiguous, and is usually viewed differently by different people. So when an organization has a “culture problem,” where do you start? The low-hanging fruit is to assume that the problem resides with specific individuals. The reality is that cultural problems typically start and fester within the overarching ecosystem of an agency.
At Cityfi, we’ve led and supported organizational assessment initiatives over the years for public sector agencies at some of the largest cities in the country. One of the most crucial lessons I’ve learned from this work is that cultural problems can have their root in specific leadership or individuals driving a particular environment, but more often than not, cultural challenges are due to a lack of clarity. Conducting an organizational assessment is a bit like being a sleuth, where you have a mission to unearth the areas where that lack of clarity resides. By doing so, we can figure out where people lose agency, perceived value, and motivation: factors that inherently affect their happiness and, therefore, their ability to innovate, think creatively, problem solve, and ultimately progress in their roles.
Cityfi looks for this lack of clarity in a variety of places - policy, processes, communication protocols, workflow procedures, definitions of roles, and responsibilities. Sometimes lack of clarity does reside at the top, where the values and/or goals of an organization are not articulated in a way that motivates staff, articulates their role in meeting those goals, and generates their buy-in.
As an example of organizational lack of clarity, Cityfi recently conducted an assessment for a major transit agency where a division had a “culture of long hours.” But when parsed apart, it became clear that a large part of what created long hours was inefficiencies in decision-making, lack of role definition around who was doing what, and underutilized technological systems that could support more efficient work. Together, these components are indeed a “cultural problem.” However, when individual factors are identified and tackled one-by-one, staff overtime can improve, and therefore so can the “culture.”
While assessing an agency’s organizational structure, processes, and systems is much less sexy compared to the programs and initiatives that an agency is deploying on-the-ground and in our cities, what has shown to be true is that without having one’s “house in order,” an agency’s ability to meet its goals for the community is compromised. Successful outcomes truly do start with having the right organizational structure, systems, and processes in place so that staff find meaning, purpose and ease in their work, and therefore, are motivated to deliver for cities.
Communicating Change: Bringing People Along and Building Buy-In
Image Source: Getty Images
In a past Cityfi blog post, I wrote about culture change as the often-overlooked driver of successful innovation. The lesson holds truer than ever: shifting priorities and building capacity isn’t just about adopting new technologies - it’s about people, politics, and persistence.
The truth is that meaningful change takes time. It requires risk-taking, a willingness to make mistakes, and the humility to own those mistakes and pivot. The City of Elk Grove’s four-year old Connected Elk Grove initiative is a powerful example. They’ve been methodical, consistent, and grounded in values, allowing the program to stay the course through radical global shifts, evolving local priorities, and staffing changes. The steady internal commitment and follow through is making long-term transformation possible.
At Cityfi, we’ve also seen how collaboration in cohorts can help mitigate risk and accelerate learning. Our work with the Los Angeles Cleantech Incubator’s Zero Emissions Delivery cohort showed how collective experimentation allows organizations to test ideas, share insights, and normalize failure as part of the process. These environments build confidence among stakeholders and create space for innovation that might otherwise feel too risky.
Of course, politics are never far from the surface. The core of the work may remain the same, but the way it is communicated often has to shift with the audience or moment. We’ve all been reminded in recent years that language, framing, and timing can be as important as the policy or project itself. Ignoring politics rarely works; navigating them thoughtfully is part of building buy-in. That’s why Cityfi is supporting the development of Common Sense Mobility, an organization designed to help cities tackle the politics of congestion pricing directly. It’s not just about crafting smart policy; it’s about building coalitions, reframing the conversation around benefits, and supporting candidates willing to champion transformative change.
Congestion pricing is a perfect example of this challenge. It asks people to shift deeply ingrained behaviors, how they move through their city every day, so the framing has to emphasize what’s gained, not just what’s restricted. Cleaner air, faster and more reliable transit, safer streets, healthier communities: these are the outcomes that make the case. Building buy-in means making the tent bigger, aligning diverse stakeholders, making the case to new funders, and resisting the temptation to focus only on what might be taken away. And as with any transformative effort, we have to remember: change doesn’t happen overnight. It happens step by step: through persistence, adaptation, and the long-term commitment to bringing people along.
Designing for Efficiency: Process, Tools, and Ownership
Efficiency is one of those words that gets tossed around easily, but what do we really mean by it? For some organizations, efficiency is about cutting costs or speeding up delivery. For others, it’s about creating the space for staff to focus on higher-value work, whether that means solving problems, thinking strategically, or being more creative. At its core, efficiency is not just about doing things faster, but about making sure our processes and tools serve the mission of the institution and the people who carry it forward.
Too often, organizations equate efficiency with working harder. But the real opportunity lies in designing processes that work smarter. Every institution runs on a set of repetitive tasks: reporting, approvals, communications, compliance checks. These activities are necessary, but we rarely pause to ask: What is the real aim of this task? Is there a better way to achieve the same result?
The starting point is simple: identify the processes that take up the most staff time. From there, evaluate whether they are achieving their intended outcomes. If they are, document them so they’re clear and repeatable. The next step is to ask whether these processes could be streamlined, delegated, or automated. This is where technology, and increasingly AI, can play a powerful role.
Recent studies show that organizations across sectors are finding success in automating high-volume administrative tasks, from permit reviews in cities like Honolulu to customer inquiries managed by AI chatbots. The goal isn’t to replace people, but to free them from routine, repetitive work so they can focus on tasks that require human judgment, creativity, and care. AI is not a silver bullet, but when applied thoughtfully, it can transform the day-to-day experience of staff and expand organizational capacity.
Designing for efficiency is not about stripping work to its bare minimum. It’s about reclaiming time and energy for the work that matters most.
At Cityfi, we help organizations take this journey, rethinking processes, identifying opportunities for streamlining, and building confidence in how to integrate new tools like AI. If your institution is ready to create more space for creativity, innovation, and impact, we would love to talk with you!
Making Space to Think Big: Why Teams Need Time to Imagine
“Creativity is not just for artists. It’s for businesspeople looking for a new way to close a sale; it’s for engineers trying to solve a problem; it’s for parents who want their children to see the world in more than one way.”
— Twyla Tharp, The Creative Habit
Teams often get stuck not because they lack creativity, but because the systems around them don’t allow it. Making space to think bigger means intentionally designing environments and rhythms that encourage expansive thinking, collaboration, and experimentation. It’s about building “sandboxes” where ideas can be explored, tested, and refined: without judgment or immediate pressure to deliver.
The challenge isn’t that teams aren’t creative, it’s that they rarely have the room to be. Too often, team members are trapped in the nonstop flow of meetings, deadlines, and daily operations. How many times have you heard: “I’m too busy to think about something else”? Creative thinking is pushed aside, seen as indulgent or disconnected from near-term results. But in reality, creativity is a long-term investment to better outcomes, stronger team dynamics, and smarter processes.
Sandboxes don’t need to be too fancy. At Cityfi, we intentionally create space for this kind of thinking. Every week, we set aside 25 minutes for what we call a “Project Hold”: a team-wide meeting focused on reflection, skill-sharing, or collaborative problem-solving. The meeting is led, structured, and facilitated by one of our team members and has become essential to how we grow ideas and refine our practice.
With our clients, we’ve used sandboxes in various ways. To help US cities prepare for the complex mobility challenges of hosting the 2026 FIFA World Cup, we worked with ITS America to convene a three-part workshop series using design thinking principles. These sessions gave public agencies the space to explore big, hairy challenges and co-develop problem statements, which were then pitched to the private sector to source bold, ready-to-deploy solutions. After supporting an organization in developing its Strategic Plan and Action Agenda, we designed a workshop series to connect day-to-day work with the plan’s long-term vision. This intentional “sandbox” helped team members step out of business-as-usual thinking and identify new ways to work toward shared goals. Following the launch of Connected Elk Grove, we established recurring advisory sessions where the City’s team could bring forward ideas in real time. These sessions became a creative space to draft game plans, pressure-test initiatives, and explore opportunities beyond the week-to-week agenda.
Creating space to think bigger isn’t about clearing your calendar and hoping ideas appear. It requires intention, structure, and care. Here are a few key ingredients:
Purposeful Design: Start with a goal: learning, exploring, questioning, and give it structure. Guardrails help focus creativity.
Time + Space: Block off time, even just 30 minutes. Create no-meeting zones or “quiet hours” to give teams breathing room.
Foster a culture of “yes, and…”: Build space for ideas to be shared freely, and all voices, across levels, to be welcomed.
Tools + Facilitation: Use design thinking methods, mapping exercises, or creative prompts to help surface ideas and connections. Reach out if you are interested and would like us to share more facilitation tips!
Making space to think bigger isn’t additional work, it’s essential for individual and collective growth. It’s where vision is built, strategies are challenged, and new ideas take root. The sandbox might look different from place to place, but the goal is always the same: make room for what’s possible.
How Clear Vision, Processes, and Tools Drive Special Event Mobility Success
Image Source: Seattle Department of Transportation
By Monique Ho
When big events jam thousands of people into dense urban districts, the first instinct is often to blame “organizational culture” for operational hiccups: slow decisions, conflicting priorities, or last-minute scrambles. But culture isn’t an unchangeable force. What truly moves the needle is clarity of vision, clearly defined roles, consistent communication, and the disciplined use of tools and processes.
Take the 2023 MLB All-Star Week at Seattle’s T-Mobile Park. Facing severe congestion, pedestrian safety issues, and free-for-all rideshare activity, stadium partners and city agencies could have written it off as a coordination problem. Instead, they convened a cross-sector team, including several groups within the Seattle Department of Transportation, private mobility operators, local business improvement districts, enforcement personnel, and property owners to co-create an actionable operations plan. With Cityfi’s support, they aligned on detailed routing, access, and staging protocols for rideshare operations; embedded customized geofencing and in-app messaging with several rideshare companies; and activated designated pickup zones with improved stadium area wayfinding and low-cost placemaking. The result: safer streets, predictable passenger flows, and a better fan experience proven through targeted pilots and shared evaluation metrics.
Atlanta’s Downtown Stadium Area also faced similar pressures, with unregulated rideshare spilling into surrounding neighborhoods. Instead of focusing on the different objectives between venues, city agencies, and private developers, stakeholders committed to building shared tools and governance, and refocused cross-sector coordination around shared outcomes. Cityfi convened stadium partners with private rideshare companies to tailor geofencing and routing and stress-tested strategies against different scenarios (e.g., single event days, dual event days, and major sporting events) through a multi-week pilot. The framework positioned Atlanta to tackle a range of events from smaller concerts to FIFA World Cup crowds, while laying groundwork for long-term community access.
These cases show that success in special event and venue operations is about fixing processes. Clear roles, aligned partners, tactical pilots, and modern tools replace guesswork with clearer outcomes. When these elements come together, cross-sector teams can operate more efficiently, streets are made safer, and attendees enjoy a seamless experience.
The Cityfi Cluster #5
By Ryan Parzick
Ever play the New York Times Connections game? Here is our own Cityfi version for you to play! If you haven’t played before, that’s OK. The rules are simple, but hopefully, solving the game is not! The challenge: group the 16 words into 4 groups of 4. Each group has a unifying theme. You get one shot, so make it count. If you think you have the correct solution, please email us with your 4 groups (you must provide the unifying theme) and the 4 words contained in each theme. An example of a unifying theme could be “Types of Animals” containing the words: “dog,” “cat,” “rabbit,” “deer.” We’ll keep score throughout the year to crown the 2025 Cityfi Cluster Champion. The answer will be posted in our next newsletter. If you want your score to count, please submit your answer before September 26th.
Last month’s solutions are:
Beach_____ (words that start with “beach”): Wear, Ball, Front, Comber
Words associated with Testing: Pilot, Prototype, Iteration, Sandbox
Parts of City: Building, Crosswalk, Sidewalk, Skyline
Uses of the Curb: Pickup, Loading, Dining, Parking
Where in the World is Cityfi?
Check out where Cityfi will be in the upcoming weeks. We may be speaking at conferences, leading workshops, hosting events, and/or actively engaging in collaborative learning within the community. We would love to see you.
ITS World Congress - Atlanta, GA - August 24 - 28
Partner Karina Ricks will be in Atlanta with the ITS crew and would love for you to come say hello. Better yet, come check out her panel and then say hello afterwards! See below for details.
Building Blocks for CCAM Deployment - Sunday, August 24th (2:45 PM - 3:45PM)
The deployment of Connected, Cooperative, and Automated Mobility (CCAM) has progressed more slowly than initially anticipated, with significant variation across use cases. This delay stems not only from technological challenges but also from the complexity of integrating Automated Vehicles (AVs) into existing transport systems. Key barriers include regulatory and safety concerns, limited public trust, insufficient understanding of AV potential among decision-makers, and a lack of evidence on societal and economic benefits.
While some major cities are making strides—establishing infrastructure, launching robotaxi and shuttle pilots, and incorporating these services into urban mobility plans—smaller cities and rural areas often lack the resources, expertise, and guidance to follow suit. To accelerate deployment, fostering collaboration among stakeholders and sharing best practices within the CCAM implementers community is crucial. This session will explore the critical building blocks for deploying AV services, offering practical insights and strategies to inform decision-making and support a broader, more equitable rollout of CCAM solutions.
TechBBQ 2025 - Copenhagen, DK - August 27 - 28
Both of our Senior Principals, Camron Bridgford and Evan Costagliola, are meeting up in Copenhagen for a large tech summit which features BBQ - such a great combination! TechBBQ is a major gathering of the startup and innovation ecosystem in Scandinavia, where our team will be helping further the discussion of how cities and tech startups can work with each other in a mutually beneficial way. If you are in the mood for some good food and conversations while in the area, let Camron and Evan know you will be there.
Chicago City Builders Book Club - Chicago, IL - end of September
If you live in Chicago, check out the Cityfi sponsored Chicago City Builders Book Club typically meeting up around every 6 weeks near The Loop. There’s wine. There’s great conversation. There’s zero pretense.
Principal Marla Westervelt co-hosts this book club where they bring together professional city builders to discuss Chicago-centric books that explore local urban and political issues. The upcoming meetup will discuss Don't Make No Waves...Don't Back No Losers: An Insiders' Analysis of the Daley Machine. Exact date and location are to be determined, so check out their LinkedIn page for updates.
What We’re Reading
Articles handpicked by the Cityfi team we have found interesting:
City Planning: What if L.A.’s so-called flaws were underappreciated assets rather than liabilities?
Transit: Denver Transit Agency Will Subsidize First Mile of Shared Scooter Trips
Resiliency: ‘Sponge City’: Copenhagen Adapts to a Wetter Future
Digital Transformation: NYC's tree census set to branch out by using high-tech 3D scanners
Job Openings
Are you exploring opportunities for your next role? Check out these positions and contact us at info@cityfi.co to learn more!
NYC DOT’s Department of Sustainable Delivery
All Things Cityfi
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